Reacción #157745

Ecuación de reacción

Potassium t-butoxide

bromocyclopropane

2-methylbenzenethiol

→

1-(cyclopropylsulfanyl)-2-methylbenzene

Disolventes

dimethyl sulfoxide

brine

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe reaction solution was cooled to room temperature
2. 2
   Extracciónfollowed by extraction with ethyl acetate
3. 3
   SecadoThe organic layer was dried over anhydrous magnesium sulfate
4. 4
   Filtraciónfiltered
5. 5
   OtroThe solvent was then evaporated under reduced pressure
6. 6
   OtroThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1)

Procedimiento

Potassium t-butoxide (994 mg) and bromocyclopropane (2.92 g) were added to a solution of 2-methylbenzenethiol (1.05 g) in dimethyl sulfoxide (10 mL), and the mixture was stirred at 100° C. for 9.5 hours. The reaction solution was cooled to room temperature and brine was added, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and filtered. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1) to give 1-(cyclopropylsulfanyl)-2-methylbenzene as an orange oil (1.41 g, quant.).

Fuente